Cyclic olefin-based polymers produced by using cyclic olefins as monomers have alicyclic structures in their main chain skeletons. Hence, such a cyclic olefin-based polymer is more likely to be amorphous, exhibits an excellent transparency and heat resistance, has a small photo-elastic coefficient, and also has such properties as a low water absorbing property, acid resistance, alkaline resistance, and a high electrical insulation property. For this reason, use of the cyclic olefin-based polymers has been examined in applications such as display applications (retardation films, diffusion films, liquid-crystal substrates, films for touch panels, light guide plates, protection films for polarizing plates, and the like), optical lens applications, optical disk applications (CD, MD, CD-R, DVD, and the like), optical fiber applications, optical film/sheet applications, and sealing applications for optical semiconductors. Of such cyclic olefin-based polymers, hydrogenated products of cyclic olefin-based polymers obtained by ring opening metathesis polymerization of norbornene derivatives are particularly known to exhibit excellent transparency and heat resistance, and to have a characteristic of a small photo-elastic constant. Hence, such a hydrogenated product, as well as polycarbonate, has been used for retardation films for liquid crystal displays (LCD) and the like. For this reason, development of cyclic olefin-based polymers obtained by using norbornene derivatives has been actively conducted. Under such circumstances, cyclic olefin-based polymers having various structures have been developed. In particular, cyclic olefin-based polymers having a spiro structure, which is one of the cardo structures, and the like have attracted attention, because desired birefringence and wavelength dependence, which are required for retardation films for LCDs, can be controlled freely.
As a method for producing a norbornene derivative having a specific structure such as the spiro-type structure, for example, Japanese Unexamined Patent Application Publication No. 2006-189474 (PTL 1) discloses a method for producing a norbornene derivative having a spiro-type structure, comprising carrying out a Diels-Alder reaction of a vinyl ketone synthesized by a Mannich reaction or the like with cyclopentadiene (Total yield: 53%). Meanwhile, Japanese Unexamined Patent Application Publication No. 2008-7733 (PTL 2) discloses a method for producing a norbornene derivative having a spiro-type structure by utilizing a Diels-Alder addition reaction of cyclopentadiene with an olefin compound (the yield of the vinyl ketone is not shown). In addition, Bulletin de la Societe Chimique de France (5) published in 1966, pages 1693 to 1698 (NPL 1) discloses a method for producing a norbornene having a spiro-type structure, comprising: synthesizing a Mannich base (N,N-dimethylamino methyl-α-tetralone) (yield: 65%) by reacting α-tetralone, which is a cyclic ketone, and dimethylamine hydrochloride in a 35% aqueous formalin solution; and then reacting the Mannich base with cyclopentadiene. Furthermore, Chem. Ber. vol. 117 published in 1984, pages 682 to 693 (NPL 2) discloses a method for producing a norbornene derivative having a spiro-type structure, comprising: synthesizing a Mannich base from a cyclic ketone such as cyclopentanone, cyclohexanone, 1-indanone, or 1-benzosuberone in a usual manner; and then reacting the Mannich base and cyclopentadiene. However, none of the conventional methods for producing a norbornene derivative described in PTLs 1 and 2 and NPLs 1 and 2 is necessarily sufficient from the viewpoint of producing the norbornene derivative in a sufficient yield.